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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o825.
Published online 2009 March 25. doi:  10.1107/S1600536809009635
PMCID: PMC2968933

tert-Butyl 3-[2,2-bis­(ethoxy­carbon­yl)­vinyl]-2-methyl-1H-indole-1-carboxyl­ate

Abstract

In the title compound, C22H27NO6, the indole ring system is planar and the ethoxy­carbonyl chains adopt extended conformations. In the crystal, inversion dimers linked by pairs of C—H(...)O hydrogen bonds occur, resulting in R 2 2(16) dimers, which are inter­linked into a chain propagating along the a axis by π–π stacking inter­actions [centroid–centroid distance 3.5916 (9) Å].

Related literature

For general background, see: Hood et al. (1992 [triangle]); Cram et al. (2001 [triangle]). For hybridization, see: Beddoes et al. (1986 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-0o825-scheme1.jpg

Experimental

Crystal data

  • C22H27NO6
  • M r = 401.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o825-efi1.jpg
  • a = 9.1933 (3) Å
  • b = 21.8495 (6) Å
  • c = 10.7676 (3) Å
  • β = 96.510 (2)°
  • V = 2148.93 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.978, T max = 0.982
  • 24241 measured reflections
  • 4766 independent reflections
  • 3534 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.134
  • S = 1.04
  • 4766 reflections
  • 286 parameters
  • 28 restraints
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009635/ci2766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009635/ci2766Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

MT thanks Dr Babu Varghese, SAIF, IIT–Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Indole-carboxylate derivatives are known to be sensitive to N-methyl-D-aspartate (NMDA) antagonists and capable of reducing the damage associated with an ischemic insult in Mongolian gerbil hippocampal neurons (Hood et al., 1992). Also the naturally occurring indole compounds can induce cell cycle to arrest the human breast cancer cells (Cram et al., 2001).

The indole ring system is planar and both ethoxycarbonyl groups adopt extended conformation as can be seen from the torsion angles C17—O3—C18—C19 [169.7 (2)°], C18—O3—C17—C16 [-177.6 (2)°], C21A/C21B—O5—C20—C16 [-165.5 (4)° /170.9 (5)°] and C20—O5—C21A/C21B—C22A/C22B [-105.2 (6)° / -176.8 (5)°]. The sum of bond angles around N1 [359.96°] indicates that atom N1 exhibits sp2 hybridization (Beddoes et al., 1986). In the tert-butoxycarbonyl group, the three C—C bond lengths lie between 1.501 (3) Å and 1.507 (3) Å, while the three tert-butyl C—C—C angles are in the range 110.6 (2)°–113.1 (2)°, indicating a slight opening up from the ideal tetrahedral value.

In the crystal structure, the molecules form R22(16) dimers through paired C23—H23C···O6 hydrogen bonds (Bernstein et al., 1995). A π-π stacking interaction is observed between pyrrole rings of moloecules at (x, y, z) and (2 - x, -y, -z), with a centroid to centroid distance of 3.5916 (9) Å.

Experimental

To a solution of tert-butyl 3-formyl-2-methyl-1H-indole-1-carboxylate (4 g, 15.44 mmol) in dry benzene (120 ml), diethylmalonate (2.8 ml, 18.53 mmol), piperidine (6 drops) and acetic acid (3 drops) were added and refluxed in Dean-Stark apparatus for 48 h. Removal of solvent followed by recrystallization from methanol afforded the product as brown crystals.

Refinement

The ethyl C atoms of the ethoxycarbonyl group are disordered over two positions (C21A/C22A and C21B/C22B) with refined occupancies of 0.58 (1) and 0.42 (1). The corresponding O—C and C—C bond distances involving the disordered atoms were restrained to 1.45 (1) Å and 1.53 (1) Å, respectively, and also their Uij parameters were restrained to an approximate isotropic behaviour. H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2–1.5(methyl)Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity. Both disorder components are shown.
Fig. 2.
The packing of the molecules viewed down c axis, showing C—H···O interactions (dashed lines).

Crystal data

C22H27NO6F(000) = 856
Mr = 401.45Dx = 1.241 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4766 reflections
a = 9.1933 (3) Åθ = 2.1–27.2°
b = 21.8495 (6) ŵ = 0.09 mm1
c = 10.7676 (3) ÅT = 293 K
β = 96.510 (2)°Block, brown
V = 2148.93 (11) Å30.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII area-detector diffractometer4766 independent reflections
Radiation source: fine-focus sealed tube3534 reflections with I > 2σ(I)
graphiteRint = 0.030
ω and [var phi] scansθmax = 27.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −11→11
Tmin = 0.978, Tmax = 0.982k = −27→28
24241 measured reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0561P)2 + 0.6467P] where P = (Fo2 + 2Fc2)/3
4766 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.25 e Å3
28 restraintsΔρmin = −0.28 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.11345 (14)0.63504 (5)0.68637 (11)0.0507 (3)
O20.00198 (17)0.68868 (6)0.52523 (12)0.0639 (4)
O30.39872 (13)0.51263 (5)0.24128 (12)0.0508 (3)
O40.34111 (19)0.43222 (8)0.11765 (15)0.0797 (5)
O50.3720 (2)0.33528 (7)0.4564 (2)0.0942 (6)
O60.49107 (19)0.34337 (7)0.2910 (2)0.0947 (6)
N10.09171 (14)0.59345 (5)0.49600 (12)0.0370 (3)
C20.03282 (17)0.58731 (7)0.37025 (14)0.0378 (3)
C3−0.06844 (19)0.62313 (8)0.29745 (16)0.0482 (4)
H3−0.10610.65870.32870.058*
C4−0.1107 (2)0.60389 (9)0.17750 (17)0.0572 (5)
H4−0.17750.62730.12630.069*
C5−0.0566 (2)0.55057 (10)0.13070 (16)0.0571 (5)
H5−0.08770.53870.04900.069*
C60.0423 (2)0.51497 (9)0.20315 (16)0.0491 (4)
H60.07760.47900.17150.059*
C70.08915 (17)0.53353 (7)0.32463 (14)0.0386 (3)
C80.18327 (17)0.50633 (7)0.42574 (15)0.0381 (3)
C90.18175 (16)0.54260 (7)0.52819 (14)0.0368 (3)
C100.06355 (18)0.64434 (7)0.56895 (15)0.0425 (4)
C110.1044 (2)0.68359 (8)0.78201 (17)0.0514 (4)
C120.1872 (3)0.65426 (12)0.89548 (19)0.0792 (7)
H12A0.13990.61670.91400.119*
H12B0.18850.68150.96550.119*
H12C0.28570.64590.87920.119*
C130.1810 (2)0.74056 (9)0.7464 (2)0.0657 (5)
H13A0.27680.73020.72560.099*
H13B0.18970.76870.81530.099*
H13C0.12560.75920.67540.099*
C14−0.0535 (2)0.69411 (10)0.7993 (2)0.0672 (6)
H14A−0.10320.71200.72480.101*
H14B−0.05950.72130.86860.101*
H14C−0.09860.65580.81570.101*
C150.26345 (17)0.44895 (7)0.42693 (16)0.0431 (4)
H150.26550.42630.50020.052*
C160.33461 (18)0.42406 (7)0.33802 (17)0.0465 (4)
C170.35749 (19)0.45525 (8)0.21940 (18)0.0513 (4)
C180.4202 (3)0.55038 (11)0.1348 (2)0.0752 (6)
H18A0.33630.54740.07180.090*
H18B0.50670.53730.09810.090*
C190.4382 (4)0.61385 (13)0.1811 (3)0.1133 (11)
H19A0.34980.62700.21280.170*
H19B0.45850.64020.11390.170*
H19C0.51790.61560.24680.170*
C200.4073 (2)0.36390 (8)0.3563 (2)0.0626 (5)
C21A0.4535 (8)0.2800 (2)0.5168 (11)0.093 (2)0.580 (10)
H21A0.54730.27410.48530.111*0.580 (10)
H21B0.46840.28360.60710.111*0.580 (10)
C22A0.3500 (8)0.2300 (3)0.4765 (13)0.089 (3)0.420 (10)
H22A0.38970.19170.50810.134*0.420 (10)
H22B0.33500.22860.38690.134*0.420 (10)
H22C0.25820.23740.50840.134*0.420 (10)
C21B0.4319 (10)0.2723 (3)0.4519 (9)0.0645 (19)0.420 (10)
H21C0.39360.25110.37600.077*0.420 (10)
H21D0.53800.27240.45910.077*0.420 (10)
C22B0.3768 (8)0.2453 (3)0.5638 (9)0.096 (2)0.580 (10)
H22D0.40680.20330.57190.144*0.580 (10)
H22E0.27180.24750.55520.144*0.580 (10)
H22F0.41600.26750.63690.144*0.580 (10)
C230.26713 (19)0.53322 (8)0.65178 (16)0.0478 (4)
H23A0.32830.49780.64870.072*
H23B0.20140.52730.71390.072*
H23C0.32710.56850.67290.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0686 (8)0.0437 (6)0.0384 (6)0.0115 (6)−0.0001 (6)−0.0066 (5)
O20.0922 (10)0.0455 (7)0.0517 (8)0.0258 (7)−0.0018 (7)−0.0023 (6)
O30.0479 (7)0.0487 (7)0.0557 (8)0.0009 (5)0.0059 (6)0.0031 (5)
O40.0929 (12)0.0852 (11)0.0638 (9)−0.0061 (9)0.0205 (8)−0.0259 (8)
O50.0943 (12)0.0479 (8)0.1461 (17)0.0286 (8)0.0386 (12)0.0268 (10)
O60.0797 (11)0.0628 (10)0.1485 (17)0.0245 (8)0.0437 (11)−0.0134 (10)
N10.0403 (7)0.0349 (6)0.0353 (7)0.0041 (5)0.0019 (5)−0.0001 (5)
C20.0400 (8)0.0386 (8)0.0349 (8)0.0015 (6)0.0047 (6)0.0018 (6)
C30.0525 (10)0.0458 (9)0.0454 (10)0.0110 (7)0.0022 (8)0.0056 (7)
C40.0592 (11)0.0679 (12)0.0421 (10)0.0134 (9)−0.0045 (8)0.0110 (8)
C50.0597 (11)0.0756 (13)0.0348 (9)0.0058 (10)−0.0003 (8)−0.0023 (8)
C60.0504 (10)0.0566 (10)0.0406 (9)0.0053 (8)0.0058 (7)−0.0074 (7)
C70.0378 (8)0.0409 (8)0.0375 (8)0.0012 (6)0.0058 (6)0.0008 (6)
C80.0361 (8)0.0367 (8)0.0416 (9)0.0019 (6)0.0050 (6)0.0006 (6)
C90.0337 (7)0.0344 (7)0.0419 (8)0.0017 (6)0.0027 (6)0.0028 (6)
C100.0488 (9)0.0369 (8)0.0417 (9)0.0052 (7)0.0043 (7)−0.0016 (7)
C110.0596 (11)0.0500 (10)0.0446 (10)0.0031 (8)0.0055 (8)−0.0149 (7)
C120.1044 (18)0.0845 (16)0.0454 (11)0.0108 (14)−0.0056 (11)−0.0163 (11)
C130.0655 (13)0.0569 (11)0.0758 (14)−0.0066 (9)0.0130 (11)−0.0185 (10)
C140.0648 (13)0.0679 (13)0.0716 (14)−0.0075 (10)0.0198 (11)−0.0251 (10)
C150.0403 (8)0.0369 (8)0.0517 (10)0.0015 (6)0.0037 (7)0.0014 (7)
C160.0400 (9)0.0372 (8)0.0625 (11)0.0010 (7)0.0070 (8)−0.0074 (7)
C170.0416 (9)0.0527 (10)0.0606 (11)0.0030 (8)0.0098 (8)−0.0116 (9)
C180.0777 (15)0.0826 (16)0.0658 (14)−0.0049 (12)0.0107 (11)0.0210 (12)
C190.147 (3)0.0703 (17)0.117 (2)−0.0217 (17)−0.009 (2)0.0326 (16)
C200.0486 (10)0.0378 (9)0.1030 (17)0.0015 (8)0.0151 (11)−0.0059 (10)
C21A0.107 (4)0.057 (3)0.112 (5)0.024 (3)0.001 (4)0.002 (4)
C22A0.094 (4)0.072 (4)0.101 (6)0.004 (3)0.008 (4)0.009 (4)
C21B0.090 (4)0.038 (3)0.067 (4)0.022 (3)0.014 (3)0.011 (3)
C22B0.117 (4)0.073 (3)0.102 (5)0.028 (3)0.031 (4)0.037 (3)
C230.0466 (9)0.0463 (9)0.0477 (10)0.0074 (7)−0.0065 (7)0.0002 (7)

Geometric parameters (Å, °)

O1—C101.311 (2)C12—H12C0.96
O1—C111.4874 (19)C13—H13A0.96
O2—C101.1917 (19)C13—H13B0.96
O3—C171.323 (2)C13—H13C0.96
O3—C181.444 (2)C14—H14A0.96
O4—C171.200 (2)C14—H14B0.96
O5—C201.318 (3)C14—H14C0.96
O5—C21B1.484 (6)C15—C161.335 (2)
O5—C21A1.528 (6)C15—H150.93
O6—C201.188 (2)C16—C201.478 (2)
N1—C101.402 (2)C16—C171.484 (3)
N1—C91.4053 (19)C18—C191.477 (4)
N1—C21.4065 (19)C18—H18A0.97
C2—C31.389 (2)C18—H18B0.97
C2—C71.396 (2)C19—H19A0.96
C3—C41.372 (3)C19—H19B0.96
C3—H30.93C19—H19C0.96
C4—C51.384 (3)C21A—C22A1.481 (7)
C4—H40.93C21A—H21A0.97
C5—C61.371 (3)C21A—H21B0.97
C5—H50.93C22A—H22A0.96
C6—C71.390 (2)C22A—H22B0.96
C6—H60.93C22A—H22C0.96
C7—C81.440 (2)C21B—C22B1.482 (6)
C8—C91.360 (2)C21B—H21C0.97
C8—C151.454 (2)C21B—H21D0.97
C9—C231.481 (2)C22B—H22D0.96
C11—C131.501 (3)C22B—H22E0.96
C11—C141.502 (3)C22B—H22F0.96
C11—C121.507 (3)C23—H23A0.96
C12—H12A0.96C23—H23B0.96
C12—H12B0.96C23—H23C0.96
C10—O1—C11121.09 (13)H14A—C14—H14C109.5
C17—O3—C18117.53 (16)H14B—C14—H14C109.5
C20—O5—C21B106.6 (3)C16—C15—C8129.37 (16)
C20—O5—C21A124.6 (4)C16—C15—H15115.3
C10—N1—C9129.03 (13)C8—C15—H15115.3
C10—N1—C2122.65 (12)C15—C16—C20121.19 (18)
C9—N1—C2108.28 (12)C15—C16—C17123.98 (15)
C3—C2—C7121.85 (15)C20—C16—C17114.67 (16)
C3—C2—N1130.54 (15)O4—C17—O3124.32 (19)
C7—C2—N1107.54 (13)O4—C17—C16125.33 (18)
C4—C3—C2117.33 (16)O3—C17—C16110.35 (15)
C4—C3—H3121.3O3—C18—C19106.8 (2)
C2—C3—H3121.3O3—C18—H18A110.4
C3—C4—C5121.69 (17)C19—C18—H18A110.4
C3—C4—H4119.2O3—C18—H18B110.4
C5—C4—H4119.2C19—C18—H18B110.4
C6—C5—C4120.87 (17)H18A—C18—H18B108.6
C6—C5—H5119.6C18—C19—H19A109.5
C4—C5—H5119.6C18—C19—H19B109.5
C5—C6—C7118.98 (17)H19A—C19—H19B109.5
C5—C6—H6120.5C18—C19—H19C109.5
C7—C6—H6120.5H19A—C19—H19C109.5
C6—C7—C2119.28 (15)H19B—C19—H19C109.5
C6—C7—C8133.34 (15)O6—C20—O5122.79 (19)
C2—C7—C8107.25 (13)O6—C20—C16124.8 (2)
C9—C8—C7108.20 (13)O5—C20—C16112.41 (17)
C9—C8—C15123.19 (14)C22A—C21A—O5101.0 (5)
C7—C8—C15128.55 (15)C22A—C21A—H21A111.6
C8—C9—N1108.70 (13)O5—C21A—H21A111.6
C8—C9—C23126.54 (14)C22A—C21A—H21B111.6
N1—C9—C23124.65 (14)O5—C21A—H21B111.6
O2—C10—O1127.26 (15)H21A—C21A—H21B109.4
O2—C10—N1122.20 (15)C21A—C22A—H22A109.5
O1—C10—N1110.53 (13)C21A—C22A—H22B109.5
O1—C11—C13110.46 (15)H22A—C22A—H22B109.5
O1—C11—C14109.02 (15)C21A—C22A—H22C109.5
C13—C11—C14113.14 (17)H22A—C22A—H22C109.5
O1—C11—C12101.26 (14)H22B—C22A—H22C109.5
C13—C11—C12110.58 (18)C22B—C21B—O5100.4 (4)
C14—C11—C12111.74 (19)C22B—C21B—H21C111.7
C11—C12—H12A109.5O5—C21B—H21C111.7
C11—C12—H12B109.5C22B—C21B—H21D111.7
H12A—C12—H12B109.5O5—C21B—H21D111.7
C11—C12—H12C109.5H21C—C21B—H21D109.5
H12A—C12—H12C109.5C21B—C22B—H22D109.5
H12B—C12—H12C109.5C21B—C22B—H22E109.5
C11—C13—H13A109.5H22D—C22B—H22E109.5
C11—C13—H13B109.5C21B—C22B—H22F109.5
H13A—C13—H13B109.5H22D—C22B—H22F109.5
C11—C13—H13C109.5H22E—C22B—H22F109.5
H13A—C13—H13C109.5C9—C23—H23A109.5
H13B—C13—H13C109.5C9—C23—H23B109.5
C11—C14—H14A109.5H23A—C23—H23B109.5
C11—C14—H14B109.5C9—C23—H23C109.5
H14A—C14—H14B109.5H23A—C23—H23C109.5
C11—C14—H14C109.5H23B—C23—H23C109.5
C10—N1—C2—C3−6.4 (3)C2—N1—C10—O2−8.8 (3)
C9—N1—C2—C3175.54 (17)C9—N1—C10—O1−11.4 (2)
C10—N1—C2—C7176.75 (14)C2—N1—C10—O1171.02 (14)
C9—N1—C2—C7−1.29 (16)C10—O1—C11—C13−57.4 (2)
C7—C2—C3—C4−0.5 (3)C10—O1—C11—C1467.5 (2)
N1—C2—C3—C4−176.98 (17)C10—O1—C11—C12−174.57 (17)
C2—C3—C4—C50.8 (3)C9—C8—C15—C16−143.93 (18)
C3—C4—C5—C6−0.2 (3)C7—C8—C15—C1639.3 (3)
C4—C5—C6—C7−0.7 (3)C8—C15—C16—C20−178.54 (16)
C5—C6—C7—C20.9 (3)C8—C15—C16—C176.3 (3)
C5—C6—C7—C8176.11 (18)C18—O3—C17—O42.3 (3)
C3—C2—C7—C6−0.3 (2)C18—O3—C17—C16−177.62 (16)
N1—C2—C7—C6176.85 (14)C15—C16—C17—O4−135.4 (2)
C3—C2—C7—C8−176.65 (15)C20—C16—C17—O449.2 (3)
N1—C2—C7—C80.51 (17)C15—C16—C17—O344.5 (2)
C6—C7—C8—C9−175.13 (18)C20—C16—C17—O3−130.88 (16)
C2—C7—C8—C90.47 (18)C17—O3—C18—C19169.7 (2)
C6—C7—C8—C152.0 (3)C21B—O5—C20—O6−10.6 (5)
C2—C7—C8—C15177.64 (15)C21A—O5—C20—O613.0 (5)
C7—C8—C9—N1−1.27 (17)C21B—O5—C20—C16170.9 (5)
C15—C8—C9—N1−178.63 (14)C21A—O5—C20—C16−165.5 (4)
C7—C8—C9—C23−177.64 (15)C15—C16—C20—O6−167.6 (2)
C15—C8—C9—C235.0 (3)C17—C16—C20—O68.0 (3)
C10—N1—C9—C8−176.27 (15)C15—C16—C20—O510.9 (3)
C2—N1—C9—C81.60 (17)C17—C16—C20—O5−173.58 (18)
C10—N1—C9—C230.2 (2)C20—O5—C21A—C22A−105.2 (6)
C2—N1—C9—C23178.06 (15)C21B—O5—C21A—C22A−49.7 (9)
C11—O1—C10—O2−3.5 (3)C20—O5—C21B—C22B−176.8 (5)
C11—O1—C10—N1176.67 (14)C21A—O5—C21B—C22B48.2 (9)
C9—N1—C10—O2168.77 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C23—H23C···O6i0.962.553.503 (3)171

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2766).

References

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